For the past 50 years, Sir Paul McCartney has seemed perfectly happy to fill the world with silly love songs. While he has released a few branch-out projects, such as his electronic experiment “The Fireman” or his classical projects like the ballet “Ocean’s Kingdom,” they all somehow have the stamp of McCartney’s ‘70s band Wings and of a man set in his ways. However, in another apparent stylistic departure, Sir Paul is releasing an album almost entirely composed of jazz standards. Ill-advisedly entitled “Kisses on the Bottom,” the album appears to represent Sir Paul’s jump onto a standards-bandwagon that has gotten pretty crowded of late, as aging singer-songwriters such as Willie Nelson (“Stardust,” 1978), Rod Stewart (“It Had To Be You,” 2002), and Joni Mitchell (“Both Sides Now,” 2000) have both offered their particular take on the Great American Songbook. McCartney’s new album provides further evidence in affirming the increasingly evident yet unfortunate truth that pop singers offer very little in artistically transforming these standards.

What is motivating the pop stars of yesterday to embrace the popular songs of eighty years ago? The question is perplexing, especially when the result is as bad as “Kisses on the Bottom.” McCartney’s attempt to cross over into the genre of jazz is unrelentingly tedious. Crooning wispily over gushes of over-orchestrated strings and saccharine harp arpeggi, McCartney sounds tellingly (and given that he will be 70 this June, unsurprisingly) old, especially in the upper register. The man has made a career out of pleasant high-tenor smoothness, but this late in the game he sounds fragile and ready to snap, like an overstretched guitar string. McCartney’s attempts to vocally adapt to the style of a standards album likewise end up sounding stilted and uncomfortable; coy and nonchalant, he seems at times to be trying out his lounge-singer act rather than sentimentalizing in his usual staggeringly earnest way.

McCartney is poorly served by his choice of songs, which brings us back to the question of why pop stars are even releasing these standards albums. The lyrics are almost uniformly insipid—McCartney knows way more about writing a love song than most of the songwriters he’s covering did—which makes his choice to do the album all the more perplexing.

What are standards, even? Why do they persist? A standard is defined by the Oxford Encyclopedia of Music as “a popular song that becomes an established item in the repertory…including popular songs from the late 19th century, songs from Broadway musicals and Hollywood films.” They quickly became the staple of jazz recordings in the 1920s and ‘30s. The song “Dinah,” for example, was published in 1925, with music by Harry Akst and lyrics by Sam M. Lewis and Joe Young. It was added to the Ziegfeld musical “Kid Boots” at the 11th hour; it was not until Ethel Waters recorded it as a single later that same year that it became a hit. The lyrics are mind-numbing (“Dinah / Is there anyone finah / In the state of Carolinah?”), but all the same, dozens of popular artists recorded the song in the ensuing decades. Between Ethel Waters and Bing Crosby, very few of these artists created recordings with any redeeming features.

In sharp contrast stands Thelonious Monk’s 1964 solo piano rendition of “Dinah.” The absurd lyrics are thankfully absent, cast aside in favor of the deeper meaning and expressivity of Monk’s pianistic craftsmanship. He begins with sharp, irreverently bouncing staccato, deliberately parodying the big-band silliness of the song’s origin—Monk plays the piano more as a percussion instrument than anything, and his cheeky riffing is full of sharp, overzealous wackiness and unexpected delays. But near the end of the track, the tone shifts from mocking giddiness to quiet sincerity. Monk plays the final bars with uninhibited reverberation and an almost hymnal care—he’s transcended “Kid Boots,” the tackiness of the other recordings, and perhaps even the song itself. As a final unresolved suspension rings out, Monk crowns his achievement by trilling the top two notes on the piano with sneaky, tinny irreverence.

Thus we see the story of standards as a battleground for a contention as old as jazz itself: the polarization between the mainstream commercial entities, out for palatable schmaltz, and innovative musicians, prepared to take even the most asinine song as a template for stunningly brilliant virtuosity. Apart from a baseline of chordal complexity, there’s nothing special about these songs—in fact, most of them are nothing less than terrible if played straight, as McCartney has done in the tradition of innumerable pop stars. The artistic importance of the standard is dependent on the musicians who are able, somehow, to create something transcendent out of them. The studio musicians on “Kisses on the Bottom,” including pianist Diana Krall, are kept on an excessively tight leash by producer Tommy LiPuma, and even when guitar deity Eric Clapton makes an appearance for the McCartney original “My Valentine,” he only contributes a bit of lazy acoustic strumming. The album, as a result, is sterile. It recycles old, bad pop songs that have, in the absence of innovation, outlived their usefulness.

To be fair, McCartney could have done worse—all one has to do is listen to Willie Nelson’s rendition of “All of Me” to see that—but it’s clear that the entire concept of the pop singer-sings-standards album is misdirected. Jazz standards aren’t made immortal by the compositions themselves, but by the ingenious jazz arrengements created for them. In 1961, John Coltrane was able to take a song as whimsical as Rodgers and Hammerstein’s “My Favorite Things” and transform it into a revelation. If McCartney and Rod Stewart want sentimentality, they’d be better off to write it themselves—that’s what they’re best at anyway.